


A Case of Karaoke

by ladyofthursday, TobytheWise



Category: Supernatural
Genre: Angel Castiel (Supernatural), Bottom Dean, Curses, Dean Winchester Bears the Mark of Cain, Demon Dean Winchester, Fanart, Karaoke, M/M, Meddling, Sex Shop, Sex Toys, Sort Of, Tail Sex, Top Castiel, Wing Kink, Wing Oil, deals with death, sing offs
Language: English
Status: Completed
Published: 2018-03-02
Updated: 2018-03-02
Packaged: 2019-03-26 05:49:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,511
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13851384
Author URL: https://archiveofourown.org/users/ladyofthursday/pseuds/ladyofthursday, https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: Dean Winchester - tall, handsome, heartbreaker, incredibly talented singer, bachelor, owner of a large penis (but that last one’s a given so you don’t specifically need to mention that) - has a sudden rival during karaoke night and things are about to get…heated





	A Case of Karaoke

**Author's Note:**

> Ladyofthursday and I wrote this back and forth style on Tumblr. If you enjoyed this and want us to write more stories together let us know!! :)

TOBYTHEWISE:

Dean sits down at the bar after flawlessly performing ‘I’m too sexy’. He only had two hecklers tonight so he’ll count that as an outstanding win. Plus they were human and shut their traps real quick once he flashed his black eyes at them. Just remembering the moment of fear in their eyes brings a smile to his face.

The door of the bar swings open and two guys walk in. Dean’s interest is peaked once he sees their wings. One is shorter with six golden wings behind his back. He carries himself with an easy go lucky attitude.

But it’s the other angel that catches Dean’s eye. He holds himself stiff and proper. He’s wearing black slacks and a white button up shirt with the sleeve rolled up and the top few buttons undone. Dean wants to run his fingers through his already messed up brunette hair.

Dean’s brought back from his thoughts when Crowley grumbles beside him. “Fucking pompous ass.”

“Mmm, I’d like to pull the stick out of his ass and see if I can stick something else in there.”

Crowley turns and glares, “Is there anyone you won’t fuck, Dean?”

Dean shrugs and taps his chin like he’s thinking. “You?”

Dean turns back the the angel he has his eye on. He watches the movement of his black wings and notices the slightest blue shimmer to them. His hands itch for a feel.

Dean’s surprised when his angel walks up the the dj and hands him some cash. Then takes his place up on stage with the mic.

And before Dean knows what’s going on, music begins to blare and the guy is singing. Dean scoffs hearing the beginning to ‘Can’t stop this feeling’.

The angel on the other hand smiles a giant gummy grin and begins moving his hips to the music. By the time the chorus hits people are actually singing with him. He even hears Crowley humming along.

The second time the chorus comes around, this angel has the nerve to leave the stage with his mic and making his way through the tables. And then, he gets up onto a table in the middle of the bar and dances up there while he sings.

“Who the fuck does this guy think he is?” Dean growls. Crowley snickers beside him. His eyes flash black and his tail twitches with his agitation. Just because this guy is sexy as sin doesn’t mean he can come into Dean’s territory and steal his goddamn crowd! Dean has to wrap his tail around his thigh so he doesn’t accidentally swat anyone with it.

The angel stares right at Dean as he sings, “I got this feeling in my body!” The angel runs his hand over his torso and Dean’s blood runs hot. “I got this feeling in my body.” He quirks his eyebrow at Dean before turning and getting back up on stage. The crowd hoots and hollers when the song is finished and Dean’s anger kindles further.

Dean slams his whiskey back and shoots daggers at the angel as he sits down next to his angel friend. They both huddle down to talk and the Golden winged angel quickly looks at Dean and then back. Dean won’t stand for this. He’s just gotta figure out what to do next.

LADYOFTHURSDAY:

Cas smiles to himself as he takes a seat at the bar next to Gabriel. The archangel’s face is a picture of shock, awe and a little bit of frustration - that’ll teach him to make stupid bets.

“I believe you owe me a drink, Gabriel,” Cas smirks, as his brother grumbles.

“Jesus Cassie, where the fuck did that come from?” Gabe signals to the barman and orders two obscenely large, colourful cocktails. “You’ve got some seriously sexy moves for someone who spends half their time with a stick up their ass.”

Cas raises an eyebrow but says nothing, instead eyeing up the drink that his brother has pushed in front of him. The rim of the glass is covered in pink sugar and the drink itself is a mixture of pink, orange and yellow, with a little umbrella and several fruit pieces perched on the top.

“Gabriel, what is that?”

“Sex on the beach,” Gabe winks, “c’mon Cassie you definitely need to get laid.”

Cas rolls his eyes and shakes his head. This is Gabriel’s argument every time they come out and it’s as predictable as the ridiculous drinks. Still… Cas can’t help glancing over at the demon sat in the corner - the one who was giving him filthy looks the entire time he was singing. He wasn’t sure whether the demon wanted to kill him or fuck him, then again, can you really ever tell with demons?

Castiel tries not to stare while he sips his drink, but it’s difficult. He’s pretty sure there’s a killer body underneath that awful plaid shirt, especially given the way his jeans seem to cling to his muscular thighs. Plus, those lips; plush, pink and oh so kissable. Castiel can definitely think of several ways he’d like to put them to use!

He may be an angel, but he’s still got eyes.

The demon obviously spots him looking and gives him an appraising look that leaves Cas blushing, before shooting the angel a wink. Castiel is contemplating whether he should say something, when a familiar voice purrs behind him,

“Evening boys.”

“Meg!” Gabriel exclaims, practically launching himself off the stool at the demon, pulling her into a colossal hug. “How is my favourite troublemaker?”

“Divine darling, as always. Are you buying?” Meg answers, sliding herself onto the stool next to Castiel, sandwiching him between her and his brother. “Hey Clarence, nice moves.”

“Hello Meg,” Cas replies politely, trying not to look at her. It’s not that he doesn’t like Meg, he does. He’s run in to her enough times now for them to at least be friends, but there’s a look in her eye tonight that worries him. Meg’s plotting something and Cas is really hoping it doesn’t involve him.

“So, Clarence, did I see you eyeing up the lovely Dean over there?” Cas turns to her, mouth open in shock slightly. Was he really that obvious in looking? Meg winks at him and sucks her drink in through a straw in quite possible the dirtiest way possible.

“Oh he definitely was,” chimes in Gabriel, appearing next to Castiel like a bad smell, new drink in hand. “Cassie here is dying for a taste of that boy.”

“Gabriel…” Cas growls, but it’s useless. His brother is an ass and won’t listen, no matter what he says.

“Point proven,” Gabe smirks. “Now you’ve just gotta reel him in.”

“Don’t worry,” Meg adds, running her tongue over her painted red lips, “I know just how to press Dean’s buttons.”

Cas is just about to open his mouth to ask what on earth she’s talking about, when Meg grabs him by the waist and pulls him into a hard, open mouthed kiss.

 TOBYTHEWISE:

Dean watches the star of his future wet dreams sit down and chat with the angel he came in with. He can’t seem to make his eyes move from the scene in front of him. He watches the guy drink his fruity cocktail and thinks he’s never seen anything hotter. Who the fuck makes drinking look hot?

“Why don’t you just buy the guy a drink instead of being a creep?” Crowley asks.

Dean growls and swats Crowley with his tail. “You know I don’t fuck with angels anymore. Not after what happened with Anna and Michael. One minute they’re into it and the next they’re saying demons are disgusting and trashy. I’m not interested in being shamed for liking sex.”

He orders another whiskey from the bartender and turns to look at sex hair again. That’s when he noticed Meg. That demon likes to mess with Dean and definitely not in the sexy way. He watches as she gives him a wicked smile before pulling the angel into a dirty open mouth kiss. His face heats up as he literally sees her tongue going into his mouth.

Dean slams back his whisky before turning to Crowley, “Well, that’s my cue. See ya later.”

Dean storms out without looking at the angel again. He’d rather not see anyone tongue fucking, especially not Meg.

Of course, Dean figures that will be the end of it. Usually he sees someone he’d like to fuck, he either fucks them or forgets them. Unfortunately that doesn’t seem the be the case this time.

Every night when he closes his eyes, Dean dreams of messy bed head hair and unearthly blue eyes play in his head. He’s constantly waking up hard and wanting. He hasn’t been this horny since he was a fresh demon for Christ’s sake!

It’s been six days since his run in with that sexy ass angel and Dean is frustrated and horny and fucking sick of this! He calls up his two best friends and demands them to meet him at the bar. He has a plan to get this angel off his mind once and for all.

Dean’s on his third whiskey when Sam and Charlie finally walk into the bar. They sit down and demand Dean tell them why they’ve been summoned.

“Guys, I can’t stop thinking about some asshat angel who came in here and stole my thunder last week. I never get hung up like this. I don’t know what the hell’s going on!” His tail flicks back and forth with his desperation.

“Dean, I don’t think I’ve seen you like this before. Are you… are you in love?”

Dean actually laughs right in Charlie’s face. “What the fuck? No! I need a piece of that ass. I know once we fuck it out he won’t be on my mind anymore!”

“Alright, then why do you need us if you have this plan already?” Sam asks sarcastically.

“I need you help with my grand plan of seduction.” Dean says with giant grin and a mischievous glint in his eye. “And looky here, my target just walked in.

All three turn to look at the door where Meg and the two angels walk in together.

LADYOFTHURSDAY:

“What was that?” demands Cas, practically throwing Meg off him. He only has to glance towards the other side off the room to realise Dean’s gone. Meg smirks at him, touching up her smeared lipstick before speaking.

“Just a way to rile up Winchester,” she gives him a predatory look, “trust me he’ll come back begging for more.”

“You are aware he left during your little stunt?” Cas huffs, ignoring Gabriel’s obscene giggling from his other side. Meg just rolls her eyes.

“It’s a good thing you’re pretty Clarence, because you really are dumb sometimes!”

Castiel can’t stop thinking about her words all week, trying to figure out what she meant. He’s still trying to relate Meg’s plan, action and words together and coming up short.

What’s worse is that he can’t stop thinking about Dean. He’s never even spoken to him and yet the demon is haunting his dreams, smirking sexily at Cas and whispering filth in his ear.

By the time Saturday night rolls around again, Cas would be quite happy to forget the rest of the world existed and spend his whole evening watching Netflix and eating pizza. Unfortunately the universe has other plans.

He’s just getting comfortable when the doorbell rings. Cas groans when he realises that both Gabe and Meg have turned up on his doorstep.

“C'mon Cassie, get dressed we’re going out!”

No amount of pleading, threatening or bargaining works and somehow Cas finds himself back at the same bar as last week, another cocktail in hand.

He spots Dean in a nearby booth, this time with two others that Cas doesn’t recognize. He can’t help but smile at the sight of the demon, but then Dean catches his eye and sends him such a dirty smirk and a wink that Cas can feel his face burning. His wings twitch awkwardly simultaneously both aroused and embarrassed. Right now, Cas wishes he could hide behind them, using them to cocoon him from the world, but that hasn’t been socially acceptable since he was seven.

Instead he drains the drink in his hand and orders another, asking the barman for angel measures to make sure there’s enough alcohol in it to hit him fast! Gabriel woops as he drains the second equally quickly and he’s just ordering a third when Meg saunters up to him, smirking.

“C'mon Clarence, you’re up next,” she says, indicating the karaoke stage. “I picked this one out especially for you!”

“But I don’t sing,” Cas protests as she and Gabe shoo him over to the stage. The dj hands him a mic, indicating the screen. It’s only then that Cas sees Meg’s choice and he really, really wishes he could smite her.

‘Hot n Cold’ by Katy Perry.

Cas takes a deep breath as the music kicks in, thanking the Lord that at least he knows the lyrics.

Then he spots Dean and Meg’s plan clicks into place. This is going to be fun!

TOBYTHEWISE:

Dean can’t seem to take his eyes off of the black winged angel yet again. He growls under his breath.

Charlie grips his arm and practically squeals. “Dean! He’s so dreamy!”

Dean smirks and tries to play it cool. “I know. And just wait until you see his ass. I could bounce a quarter off that perky thing.”

“Gross, Dean!” Sam groans.

All three watch as Cas walks up on stage. The angel looks right at Dean and smirks as the music begins to play.

“So what’s your grand scheme?”

He shrugs. “I’ve decided to wing it,” Dean says as he makes his way up onto the stage.

The angel’s eyes get impossibly big in surprise and Dean gives him a wink. He grabs the second mic from the stand and saunters up close to the angel.

Dean’s mesmerized as the angel sings the first verse in his deep, raspy voice. The angel’s eyes are an unearthly shade of blue and they fill with a spark as he sings right to Dean.

“You’re wrong when it’s right! It’s black and it’s white. We fight, we break up! We kiss, we make up.” The angel shoves his finger into Dean’s chest a few times and has the nerve to make kissy lips at him. It’s so immature and dumb and so fucking sexy.

Dean rolls his eyes and lifts the mic to his lips interrupting the angel and taking over the second verse. “We used to be, just like twins. So insync.”

Dean lets himself make faces at the crowd and at the angel. As he gets to the chorus everyone’s attention is on them and Dean eats it up.

“Cause you’re hot,” he sings with a giant flirty wink. “Then you’re cold,” he sings with a shrug.

By the time the bridge comes along the two of them are right in each other’s faces singing.

They sing almost violently into their mic, “Someone call the doctor! Got a case of love bi-polar! Stuck on this rollercoaster! Can’t get off this ride!”

By the time the last chorus hits, they’re both flush and sweating. This is by far the most intense foreplay Dean’s ever experienced. The moves they’re both making and the light touches are making Dean feel light headed with pleasure.

The angel sings out the last line and pulls Dean forward so they’re chest to chest. He raises his eyebrow in the most delicious way, “you’re up then you’re down, down.”

The angel leans forward and nips Dean’s bottom lip hard and then pulls completely back to put his mic away. Dean’s frozen in place. He’s not sure he remembers a time he was ever this fucking turned on.

The angel gets down from the stage and turns back to Dean with that same damn raised eyebrow, “Well you coming or what?”

Dean scrambles to follow. He’s not sure where the angel is pulling him along to until the door of the restroom is closed and Dean’s back is firmly pressed to the door.

The angel is suddenly on him. They’re kissing and the kiss is absolutely brutal. All teeth and tongue and Dean lets out a guttural groan.

When he pulls back, the angel just detures and begins kissing down Dean’s jaw and neck. “Oh, fuck!”

Dean thrusts his hips forward and moans when he feels an answering erection in the angel’s pants. He pushes the angel further into the bathroom until he has him pinned to the sink counter.

“What’s your name, angel?” Dean whispers as he lightly touches the angel’s right wing.

The angel groans and answer, “Cas.”

Dean’s cock hardens further hearing that deep voice. “I’m Dean,” he says before diving right back into kissing Cas and fisting a handful of feathers. He lightly rubs the front of Cas’s slacks with his tail and loves the feel of the bulge he finds. He’s so fucking horny he’s lightheaded.

Suddenly the door of the bathroom slams open and they both fly apart like they’d been electrocuted. Dean discretely adjusts the front of his jeans and looks to see who the hell he’s gonna murder.

“What the fuck, Sammy!” Dean groans and runs his fingers through his hair. When he turns back he sees he’s alone in the bathroom with Sam.

“Goddamn it!” He yelled. So much for a quick fuck and moving on! What the hell is Dean supposed to do now?

LADYOFTHURSDAY:

_ >> Message from Gabriel: Emergency at shop get ass here asap _

Castiel grumbled to himself as he read the message again, before pulling on his shoes and grabbing his car keys. He wondered idly what Gabriel meant by emergency - in Gabriel’s world that could mean anything from a fire to the fact that he had dinner plans with Balthazar and had forgotten to get someone to cover the evening. It was probably the latter.

Cas sighed as he pulled out of the drive and onto the main road, winding his way towards the edge of town. He really needed to tell Gabe to get his act together and hire more staff. Thank god it was summer vacation and the university was closed, at least it meant none of his students would see him. That was the last thing he needed.

Why, oh why did Gabriel have to run a sex store?

The twinkling neon of ‘Angel’s Delight’ beckoned him into the car park and Cas sat there for a minute, wondering what fresh hell he was about to experience in the name of family. Last time Gabriel had done this, Castiel had spent the entire afternoon helping his brother arrange a display of dildos.

There was a rather lovely classic Chevrolet that was parked in front of the store, tonight, that Cas couldn’t help admire as he trudged towards the door. It must be a customers, because it certainly wasn’t his brother’s.

The door swung open easily and Castiel found himself face to face with the smirking faces of Balthazar and Gabriel.

“What do you want Gabe?” Castiel asked, wearily. “What’s so important that you had to drag me out of the house again?”

“Well, we have plans,” Balthazar smiled, “and we forgot to ask Anna to stay late. Would you be a doll and cover for us? It’ll only be for an hour or two. You can close early if you have to.” The angel produced his best pouting smile, fluttering his lashes and Cas rolled his eyes. “Your brother and I are simply desperate for some fun.”

“Fine,” snapped Cas, “but you both owe me. And Gabe?” he added to his quickly departing brother, “this time, you’re paying me. I’ll take my wages out the till.”

Gabriel looked like he might argue for a minute, but obviously decided it wasn’t worth it. Instead he shot Cas a wicked smile and winked.  

“Have fun, Cassie.”  

Castiel shook his head, slipping behind the counter and pulling off his jacket. The store was pretty quiet, a few couples wandering around together and the odd individual, but no one who wanted his attention. Pulling out his phone, he seated himself on the stool behind the till and opened the kindle app, hoping to lose himself in Santino Hassell’s _Illegal Contact_.

Still as he opened the app, his thoughts drifted back to last weekend and his impromptu make-out with Dean. It still made his face flush to think about it - the whiskey rich taste of his tongue, the caress of Dean’s tail across his erection, the determined way the demon had grabbed his wings - it had almost made Cas come on the spot.

Somehow, he’d found himself at home - jerking off angrily in the shower, with no real memory of how he’d got there. Cas assumed he’d flown, disappearing as soon as Dean’s friend barged in on them.

He still wasn’t sure what had caused him to flee. Shame, maybe, or fear. A fear that after a quick fuck in the bathroom, Dean would have cast him aside like a used rag. Demons didn’t usually tend to be relationship people.

“Shit.”

The familiar voice made Cas jump, sliding off the small seat in shock. Dean was stood at the end of the nearest aisle, full basket in hand, an expression of shock plastered all over his face.

“Hello Dean,” Cas muttered, face burning and he internally cursed. He hadn’t seen Dean come in while he was here… Gabriel must have known! Castiel swore internally that he would get revenge on his brother if it was the last thing he did. Still he couldn’t do anything now, so instead he added, “it’s nice to see you again.”  

“Yeah… um,” Dean paused, as if embarrassed. “I didn’t know you worked here.”

“I don’t,” Cas said, trying to maintain some of his dignity, despite the fact he could feel it draining away very quickly. “My brother and his boyfriend own the store, I’m just covering for them.”

“Oh,” Dean added, and Cas noticed his tail was twitching violently. “I’ll just…”

“It’s fine, I can put it through.” Cas gestured at the basket, pulling a dark bag from under the counter. “Don’t worry, it’s nothing I’ve not seen before.”

The demon set the basket on the counter, almost shyly, and stared at the space of wall behind Castiel’s head, attempting to feign an air of nonchalance.

“So, your brother?”

“Yes, Gabriel, you’ve seen him at the bar. He’s the archangel,” Cas said, trying not to pay too much attention to the toys, lube and boxes of condoms in Dean’s basket. The bottle of synthetic angel wing oil caught his eye though… was Dean still thinking about him?

“An archangel runs a dirty store?”

Cas chuckled and nodded, “there’s a reason our mother doesn’t speak to him anymore.”

“I get that.”

Another silence, thick with awkwardness.

“Listen, Dean,” Cas said, deliberately looking down at the till, “I’m sorry about last week. I panicked when your friend-”

“Brother, he’s my kid brother.”

“Oh… well, I just wanted to say that I’m sorry.” Cas looked up, smiling shyly as he caught the demon’s eye. “I was wondering, would you like to get dinner sometime?”

TOBYTHEWISE:

Dean spends 45 minutes sniffing synthetic wing oil. He just cannot seem to get Cas off his mind. Every night he thinks about those precious moments he had that angel in his grasp and he plays every possible scenario in his head as he touches himself.

Dean’s finally broken down and come to his usual place to find toys and lube. As he cruises through the shelves he throws anything that reminds him of the angel into his basket. The dildo he picked? Picked it because it was the same color as those beautiful black wings. The lube he picked? The container was the same shade of blue as Cas’s eyes. The condoms? Though Dean’s always been the king of one night stands, he hasn’t been able to bring himself to take anyone home who isn’t Cas. He literally throws them into his basket because that’s just what he always gets. Plus, it never hurts to be prepared.

And now, he stands at the synthetic angel wing oil shelf looking for the perfect scent. God, there’s so many….. finally he finds the one that matches closest to what Cas smells like and smiles knowing what his plans for the night are…. or maybe not?

“Shit.” How can this be? Is Dean really this big of a dumbass that he didn’t even know Cas was working?

Dean feels his cheeks heat as Cas scans his various toys and things and prays he doesn’t put together how they’re all basically based off of him!

“Would you like to get dinner sometime?”

Oh god! Deans brain feels like it’s malfunctioning. It’s shouting no, no, no, no! At the same time that it’s screaming say yes you idiot!!

“Yes” He croaks out. Dean clears his throat and tries again. “I’d like that.” Then he pauses and asks, “Like right now?”

Cas smiles and it makes Dean’s insides feel all gooey. Gross. Demons don’t feel like this!

“I have to close up the shop. Can you meet back here in an hour?”

“Okay. Sounds good, Cas. I’ll see you in an hour.”

Dean turns and starts walking out before he can say anything stupid. As he gets to the door he hears Cas calling his name. He stops and turns back and he feels like cheeks warm again.

“Here, you forgot this,” Cas says as he hands Dean his bag of goodies.

“Right. Thanks.”

This time Dean practically runs out of the store. He feels like such an idiot but also euphoric. He’s got a date. God, he hasn’t gone on a date in…… well, never? Shit!

Dean gets into his Impala and speeds towards his house. At a stop light he texts Charlie to meet him at his house. When he pulls up, he sees her car’s already there and he breathes a sigh of relief. She’ll know what to do.

As he walks inside, Charlie is on him like a hawk. “Is this about Cas? Pppllllease tell me it's about Mr Dreamy!” She grabs the bag from his hand, “And what’s this?”

She looks inside and throws the bag back at him, “Gross, Dean!”

Dean throws his head back and laughs but it slowly turns into a awkward forced sound when he thinks about his upcoming date.

“Fuck! I’m so screwed, Charles.”

“Tell me everything.”

“I umm, I have a, uh. I have a date.”

Charlie stops what she’s doing and openly stares at him.

“Excuse me?”

“You heard me,” Dean says annoyingly. “I have a fucking date so dress me up. I gotta go meet him so come on!”

She bursts up from her seat and runs to his room flinging clothes as she goes. She sets out a snug pair of jeans, a black tee shirt, and a red button up shirt for him to wear. With his longer hair he looks hot, if he does say so himself.

“So, are you gonna tell him?”

Dean scoffs, “Tell him what?”

Charlie sets him with a serious look. “You know what! If you’re serious about this guy, which based on your level of freak out you are serious, you should talk to him about it.”

“Charlie,”

She cuts him off. “No, Dean! Enough of this hiding behind the black eyes. He deserves to know that you’re not exactly as you appear to be! Dean, this stupid curse wasn’t even your fault!”

Dean is beginning to get angry and he turns and gets into Charlie’s face and lets his eyes slide black. “Enough! This curse was my choice to take! No one else’s! And it’s my choice who fucking knows! I asked you here for dating advice not…. not this! I’m leaving now.”

Dean storms out of the door and gets into his Impala. He lets his eyes fade back to their green and takes a deep breath. Dean clutches his forearm for a moment and rubs at the scar that’s left there from his curse. Yeah it sucks but he’d make the same decision again in a heartbeat if it kept his brother safe, alive, and human.

He drives back to the store in a fog and parks his car. Dean sits and waits for his angel to come out. He realizes the importance of this moment. Dean truly wants to woo this angel, not just fuck and forget and that scares the ever loving shit out of him. He really hopes he can figure out the etiquette for a wooing date on his own.

“Hello Dean,” says a voice to his right and dread fills his belly.

“No! Not tonight! I have a super important date, Death. Can’t you find someone else just for tonight?” Dean pleads but he already knows the answer.

“I’m sorry, but you know the rules.” And he does. So he lets Death slip the blade into his hand and waits for Death’s next order praying Cas will somehow forgive him for standing him up.

LADYOFTHURSDAY:

Castiel is so excited for his date that he’s practically vibrating. His wings flutter happily for the whole of the next hour, which may earn him the odd funny look from customers but he doesn’t care.

After closing up, Cas decides to wait outside the door so he can see Dean when he arrives. The parking lot is deserted apart from Castiel’s old Lincoln but that’s ok, he doesn’t expect Dean to be here on the dot.

So he waits. And he waits. And he waits.

After half an hour has passed, Cas is getting nervous. Has Dean forgotten? Maybe the traffic is bad?

After an hour he wishes he’d remembered to get Dean’s number.

After two hours he’s numb - tired, cranky and heartbroken. Dean’s obviously not coming. Perhaps this was just a joke to the demon? A wind up or punishment for Castiel running out on him last week.

He slowly makes his way home, eyes prickling, but he refuses to cry until he’s shut safely inside. Then the tears fall; hot, thick and fast. A sob wrenches from inside him and he curls himself on the couch, cocooning himself inside his wings. His fingers play slowly over the feathers, soothing himself with their softness.

Castiel stays there until he falls asleep.

It’s a banging that wakes him.

Cas isn’t quite sure how long he’s been out, but he’s groggy enough to need a minute or two to adjust.

The banging doesn’t stop and Castiel realises there’s someone trying to hammer down his door. Grumbling he pulls himself up, knowing full well he looks like a hot mess, and wrenches the door open.

“What?” Cas snarls, before the shock takes over. Dean is stood outside his front door, wearing a hat and carrying a giant pizza. The demon looks horribly upset, tail curled between his legs and when he looks at Cas, the angel feels his anger melting.

“Cas, I’m so sorry.” The demon’s voice sounds like it’s about to crack. “I had a family emergency and I realised I didn’t have your number and I just, I couldn’t bare you thinking I’d stood you up.”

“How did you find me?” Cas asks, still a little stunned at Dean’s determination.

“Meg,” Dean says, “I called her and begged.”

“What did that cost you?” Cas chuckles, knowing Meg will always want something. Dean grins.

“Fuck if I know! She didn’t say… it’ll be worth it though.” Castiel can feel the blush spreading across his cheeks, wings trying to hide him. Part of him thinks he shouldn’t listen, and that he should turn Dean away. The rest of him ignores that suggestion.

“Would you like to come in?” Dean nods and Cas ushers him inside, trying not to notice how good Dean’s ass looks in those tight, dark jeans.

“Nice place angel,” Dean says, admiring the room. He places the giant pizza box on the table and settles himself on the couch.

“Thank you…” Cas pauses, a little unsure what to do next. He’s never really had first dates at home before. “Would you like a beer? I’ve got Netflix as well, if you’d like to watch a movie?”

“Sounds great!” Dean smiles, visibly relaxing. Cas fetches two beers and they settle on Mad Max: Fury Road, which Cas hasn’t seen before.

The pizza is delicious. Thick crust laden with tangy sauce and a mountain of cheese and meat. It draws a happy groan from Castiel’s lips and he can’t help but notice the tiny smirk that plays across Dean’s lips. They devour the entire thing, even managing to make their way through half a tub of chocolate ice cream that Cas found in the freezer.

Castiel finds himself completely absorbed by the film, even though he probably wouldn’t have picked it for himself. As the evening progresses, Cas can’t help noticing the two of the creeping closer to each other. He feels Dean’s arm wrapping around his shoulders and then his tail snaking around Castiel’s waist.

His heart is pounding and his palms feel a little sweaty, but he can’t help be turned on the proximity of the demon sitting next to him.

“You ok?” Dean asks, shifting in his seat. Cas can’t do anything but nod. He turns to look at Dean, taking in the little details of his face - the smattering of freckles and deep bow of his lips and the way his eyelashes frame those eyes, that seem to flit from black to green.

Dean twists slightly, looking down at Cas, who blushes again. He wants to kiss Dean, he realises.

So he does.

Dean lets out a small noise of surprise as Castiel practically leaps on top of him, claiming those plush pink lips for his own. Castiel whimpers as Dean’s tongue slides into his mouth, his hands pulling Castiel closer, wriggling under Cas’s shirt to caress his skin.

Dean slides down, pulling Cas on top of him, groaning as their bodies slide together. The gentle kissing devolves into frantic making out - hands roaming, tongues and lips exploring, bodies grinding together.

Nothing else matters to Cad now, all he can think about is that he never wants Dean to leave. He wants to drag the demon upstairs and fuck until sunrise and he’s pretty sure Dean will be on board with that idea.

Cas breaks the kiss, panting hard as he locks eyes with Dean, words spilling from his lips.

“Stay tonight?”

TOBYTHEWISE:

Dean slowly wakes up surrounded by warmth. There’s a warmth in his chest he hasn’t felt in sooo long it makes his cheeks turn pink and his breath come quicker. When he opens his eyes he gets a fast track of remembering where he is.

He looks to his right and sees Cas’s face plastered to his shoulder. Dean smiles at the drool on his shirt. The angel is adorable in everything he does. He looks so beautiful like this as his face is slack and relaxed. Dean is about to bring his hand up to brush the hair from Cas’s forehead when he notices something is touching his arm. He looks down and sees he’s completely surrounded by the angel’s beautiful black wings. They’re gorgeous and soft and warm. They’re perfect.

Dean can’t stop grinning. So they didn’t have sex last night? Dean would be damned if he took things too far too fast. He actually cares about Cas and he didn’t want to hurt him. After his night with Death, he’d come here seeking forgiveness. What Dean didn’t take into consideration was all the leftover bloodlust and adrenaline from ‘his night job.’ If he wouldn’t have stopped himself when he noticed his shaky hands he might have truly hurt Cas and that’s the last thing he ever wants to do!

Dean slowly extracts himself from the wing fort Cas has him in. The angel stirs for a moment and then continues on snoring. He’s never found snoring attractive until this very moment. Huh, he really is in too deep.

Dean sighs and makes his way to the kitchen. He begins rummaging through Cas’s fridge for eggs and fixings to make omelets when the door opens. Dean’s heart drops and he gets into a protective stance.

“Father! I’m home!” Wait, what?

Dean puts the pieces together. He noticed another person in a lot of the pictures around Cas’s house but he had no idea he had a son! Nope. This isn’t gonna work. Dean will protect them with everything he has, even if it’s from himself.

“Jack? You’re home early.”

“I told you I’d be home around noon. It’s noon now. Did you have a late night with the guest in the kitchen?”

“Oh shit! Dean.”

“I’ll be in my room for a bit.”

Cas walks into the kitchen sheepishly. “Good morning, Dean.”

Dean knows he should answer but he feels frozen in place. This dueling natures at war with each other. His human side says protect, leave, keep them safe. His demon side of course says fuck it, or rather fuck him.

“I’m sorry, Cas. I, uh, shit. I can’t do this anymore. I care about you too much to see you get hurt.”

“What can’t you do? Dean, you’re not making any sense.”

Dean huffs, “Don’t you see? You have a fucking kid Cas! I won’t let you or him get hurt because of me! I’m corrupted, Cas! I’m fucking cursed!”

Dean turns to walk out the door but Cas grabs him by the shoulder and turns him back. “What does my son have to do with us? And what curse?”

Dean chews on his bottom lip. “I’m cursed,” he whispers.

“Tell me.”

When Dean looks in his eyes he sees nothing but compassion and it breaks him. “When I was 18, my mom died. My dad was an idiot and decided to summon Death.” Dean hears Cas’s sharp intake of breath but he keeps going. “Dad tried to trade my little brother’s soul for moms life. I was there and I begged Death not to do it. Said I’d do anything. He decided to grant my wish instead of dad’s.”

Dean pauses and wipes his eyes that are suspiciously moist. He hates crying. God, he hasn’t had to tell this story in ten years. “Death touched me.”

“Death touched you and you lived? How is that possible Dean?”

Dean slowly rolls up sleeve and shows Cas the scar on his forearm. It’s red and looks like a F sorta. “He left his mark, not only on my skin but my soul too. It corrupted me and I lost myself for a long time, Cas. My emotions and conscience were locked in what felt like a glass box. During that time I drank and fucked and killed and I felt no regrets.”

Dean looks down at the ground. He’s gotta push through. Once Cas knows he’ll push Dean away and they’ll be safe. “Slowly I’ve learned to feel again. I know what’s right from wrong again but I still have an unstoppable bloodlust. I crave death and blood and violence. I NEED it. So I do Death’s bidding and I collect when he tells me. I take pride and joy in ending the lives of scum that plague our world. And I don’t want you getting involved with that.”

“Dean,” Cas starts but Dean cuts him off.

“No, Cas. You don’t understand. If you stay with me I might lose myself again and hurt you and then I wouldn’t be able to live. I care too much about you! Cas, I lo-“

“Hello, Dean,” he hears behind him.

“For fuck’s same, Death! You have got the worst timing.”

Death snorts, “I don’t work on your schedule, Dean. You work on mine and I say it’s time to go. You’ve got work to do.”

Dean looks into his favorite pair of blue eyes. They’re filled with tears that slowly fall down his perfect cheeks. He tries to memorize the face he’s come to love. He never thought a demon could love but Dean supposes it just took a certain angel.

He gives Cas a sad smile and a small wave. “See what I mean?”

Dean walks over to Death and picks up the blade from Death’s outstretched hand. The steady weight of it brings him a small amount on peace. He looks at his angel one last time. “Goodbye, Cas.”

 

LADYOFTHURSDAY:

Castiel stands rooted to the spot in shock.

He wants to cry and scream and laugh and throw glasses on the floor because of-fucking-course this would happen. The universe would never allow to be happy.

Dean’s words burn in his memory: _If you stay with me I might lose myself again and hurt you and then I wouldn’t be able to live. I care too much about you!_

If only he could make Dean understand, make him see exactly what Castiel saw. Maybe then he wouldn’t be afraid.

Castiel picks up a plate from the counter and hurls it against the wall. The plate smashes with a resounding crack, pieces scattering across the floor.

“Father?” Jack’s voice startles him and Castiel jumps, socked feet slipping on the kitchen tiles. “Is everything ok?”

“No Jack, it’s not,” Cas sighs, coming back to his senses. He searches in the cupboards for something to put the shards in.

“Oh, is it to do with the demon that was here?” Jack says, squinting at Cas with that head tilt that the angel has always found adorable.

“Yes, but apparently he’s not a demon.”

“I don’t understand.”

Jack produces a broom from the cupboard and helps Cas to sweet up the mess, while Castiel relates the whole sorry affair. Plus or minus a few details he’d rather his adopted-son didn’t hear.

Jack may be off at college now, but that doesn’t mean that Cas wants him to know all the sordid details of his sex life. Not that there’s much to tell right now though. He and Dean haven’t even managed to actually get naked together yet - something that Castiel had rather been hoping to fix this morning.

“So, you’re saying that this demon, who you believe doesn’t usually like relationships, doesn’t want one with you… because of me… and because he’s scared he will hurt you,” Jack said, chewing the words over thoughtfully, leaning on the kitchen counter as Castiel began making scrambled eggs.

“Yes.”

“That sounds to me,” Jack said, “like he really cares for you. Otherwise he wouldn’t care if you got hurt.”

Castiel nodded, having already reached this conclusion himself. Still, it was nice to hear that he wasn’t the only one who thought that.

“So, what are you going to do?” added Jack, buttering some toast.

“What do you mean? I’m not going to do anything. He doesn’t want to see the truth so he just hides behind his excuses,” Cas snarked.

“So? He’s just scared, like you. You should tell him how you feel,” Jack said encouragingly. “And if not, what have you really lost?”

_My heart_ …

x

Castiel nervously sips the large Porn Star martini that Gabriel pushed into his hand, while he waits for his plan to kick into action.

“Stop worrying Cassie, everything will be fine,” Gabriel says, “once Deano gets another look at your perky ass he’s gonna be all over you.”

“What if he doesn’t come?” Cas mutters.

“Oh trust me, I don’t think there’s any chance of that happening,” Gabriel winks and Balthazar, who’s perched on the stool next to him chuckles and leans across to whisper in the archangel’s ear.

Castiel frets his way through another cocktail before he sees Dean slink into his regular booth. He’s with Charlie and Sam again, and Cas’s heart aches at the look on Dean’s face. He looks so miserable - tail hanging limply between his legs, disinterested eyes boring a hole in table and he doesn’t even attempt any sort of conversation.

Taking a deep breath, Cas makes his way up onto the stage, taking the proffered microphone and turning to face the crowd.

“Good evening, I’d like to dedicate this song to someone I met recently… Dean,” Cas looks out into the crowd and sees the demon staring, Charlie and Sam holding him in place.

“I know we haven’t known each other long, but I just wanted you to know that whatever happens, I’d rather have you… cursed or not… that anyone else… this song is for you. _Hey Jude, don’t make it bad. Take a sad song and make it better.”_

Castiel pours all his love and pain into the lyrics - he wants Dean to know how he feels, how much he cares. He remembered last night, how they’d curled up together in bed, cocooned in Castiel’s wings, sharing secrets.

_Remember to let her into your heart_

_Then you can start to make it better_

The music builds and Cas can’t stop staring at Dean. The demon’s eyes are shining with tears and Castiel’s chest feels like it’s going to explode. Slowly, he makes his way across the floor towards Dean’s table, the crowd singing along with him.

As the song fades away, Cas finds himself stood right in front of Dean, who’s looking up at him with shock and awe.

“Dean Winchester… I can’t describe the way you make me feel… I hardly know you and yet it’s like I’ve known you for a thousand years. I feel so alive when I’m with you and I don’t care if you’re cursed - we can figure it out together. I won’t let you go. There’s nobody I’d rather have, nobody at all.

Dean Winchester… I think I’m in love with you.”

There’s a moment’s silence.

Then Dean stands to pull Castiel into a kiss and the room erupts around them.

TOBYTHEWISE:

Dean stares at his beautiful angel singing the most sacred song Dean knows. The song his mother used to sing to him and his brother before she died and his whole life went to hell. This song that Cas is using to declare his love.

When Cas comes to his table and says those words out loud, I’m in love with you, Dean can’t hold back anymore. He’s out of the booth and kissing Cas like his life depends on it without another thought.

When they pull back, Cas leans in and whispers in his ear, “Picture your bedroom.”

And Dean does. When he opens his eyes again he’s standing in his bedroom in the arms of an angel. He grins and kisses Cas again. This time, pouring every ounce of emotion he can into the kiss.

Suddenly, almost as though he’s stuck my lightning, Dean leaps back and tries to steady his breathing. He’s gotta think logically, he can’t hurt Cas!

“Don’t Cas,” he says as Cas takes a step towards him. “You don’t understand how bad I truly am. I’m evil and corrupted. You don’t want me!”

Cas’s face seems to lighten and a tiny smile plays on his lips. “I do want you.” Before Dean can protest further, Cas holds out his hand and asks, “Can I show you something, Dean?”

Dean falters for a moment before nodding his head. Cas comes forward and gently turns him around. They walk so Dean is facing the mirror that’s above his dresser. It’s low enough that he can see from their waists up. Cas gently wraps his arms around Dean’s waist and rests is chin over Dean’s shoulder.

“I want you to see exactly what I see when I look at you,” the angel whispers. “Can you trust me?”

Dean nods. Cas gently takes Dean’s shirt off. Then without breaking eye contact through the mirror, Cas gently reaches his hand up and touches Dean’s forehead with his finger.

Dean gasps. He doesn’t know what he’s seeing but whatever it is takes his breath away. There’s swirls of color floating around his chest. There are swirls of different shades of green all mixed together and moving in intricate patterns. There’s small swirls of black and red that intermix with the green. It’s beautiful.

“This is your soul. There are specks of the curse that touch your soul but the goodness overtakes the bad. They all mix together to make who you are. And you’re beautiful, Dean.”

Dean watches in amazement as the colors become bolder and more vibrant as Cas talks to him.

“I love you, Dean.”

As soon as the words are out, his soul seems to become brighter and arc, almost like his soul is seeking out Cas. Trying to touch him.

“Thank you,” Dean brokenly stutters. When he brings his eyes back up, he’s met with an intense blue stare. “Cas.”

“Shh,” Cas soothes. “It’s okay. I have you now.”

Cas begins peppering Dean’s neck and shoulder with open mouth kisses and Dean wraps his tail tightly around Cas’s left thigh. He needs Cas in a way that he’s never needed anyone else before.

Dean doesn’t know where to look. He wants to watch Cas kiss him and leave marks across his skin. He also wants to watch his soul react to Cas’s closeness and see how it tries to curve towards Cas whenever the angel is touching him. It’s mesmerizing.

Cas slowly drops to his knees and kisses the dimples Dean have on his lower back. Dean can’t stop the shiver of arousal that runs through his body. He wants Cas so badly. Cas slowly undoes his jeans and slips the jeans and his boxers down his legs. He helps Dean step out of them and his shoes before standing again.

“You’re so beautiful, Dean. Every single part of you, inside and out.” Dean turns his head so they can kiss again. He can feel the hard line of Cas’s clothed erection against his ass and he groans. “I love you.”

“Cas, I haven’t said those words since before my mom died.” Dean watches as his soul dims slightly thinking about his mother. Cas has his arms around his waist again in a heartbeat, holding Dean when he needs it.

“That’s okay. I already know. You don’t have to say it.” Then he pulls back and carefully pulls his shirt off and quickly getting out of his jeans and boxers and shoes. They’re both naked and the feel of Cas’s bare skin against Dean’s back is amazing. Dean’s skin feels like it’s on fire.

Dean’s eyes meet Cas’s again in the mirror and he can’t look away. He gently pushes his hips back, silently asking for what he truly wants. Cas nods and a small smile plays on his lips as he reaches back and plays with his oil gland. Cas’s fingers come back glossy and Dean’s nose twitches with interest. Cas’s scent is a million times better than any of the synthetic stuff Dean looked at.

As Cas brings his hand down to Dean’s entrance he whispers, “Ready?”

“Yes. Please, Cas. I need you.”

Cas gently pushes his finger inside Dean and they both moan in pleasure. Dean’s never felt anything like this before. As Cas begins to work Dean open and press a second finger into Dean, they both pant while maintaining eye contact.

“Cas, that feels so incredible.” Dean says between clenched teeth. “I’ve never, oh! I’ve never done this before.”

Cas pauses his thrusting fingers in surprise. “What?”

Dean’s face burns but he continues. “I’ve never bottomed.”

Dean can see Cas’s eyes dilated further. “Oh god, Dean,” Cas groans as he continues prepping Dean’s hole. “You’re so fucking incredible. So amazing.”

Dean feels the burn of a third finger being added and he breathes through the slight pain. Pleasure takes its place quickly as Cas rubs against his prostate. Cas nips at Dean’s shoulder as he slowly pulls his fingers out.

“I’m ready,” Dean assures him. He’s more than ready. Cas slicks up his cock with more wing oil and holds his dick at Dean’s hole. He wants Cas in the most intimate way possible and his soul agrees. It brightens and flickers as Dean feels the head of Cas’s cock at his hole. He takes a deep breath to relax as Cas slowly pushes in.

“Fuck, Dean,” Cas breathes as he slowly inches forward. He’s careful and takes his time, making sure Dean can handle it.

Once Cas is completely buried inside Dean, they both take a minute to calm their panting. Dean’s never been this full, and he doesn’t just mean his ass.

“Cas,” Dean sobs as Cas begins to move, thrusting his hips slowly in and out.

Dean moves his tail up to Cas’s oil gland. After getting full of the oil, he moves it to Cas’s entrance and gently nudges it.

“What the,” Cas says in surprise.

“Is this okay?” Dean asks shyly as he watches Cas’s reaction in the mirror. “I just wanna be connected to you as much as I can.”

Cas smiles and nudges Dean’s head sideways so they can kiss again. Cas barely pulls back and nods his head before diving back into the kiss.

Dean pushes his tail forward as gently as possible and moans when it passes the tight ring of muscles. Cas’s tight heat surrounds his tail and it feels incredible. He pushes it forward and seeks out Cas’s prostate. He knows he’s found it when Cas breaks the kiss and pants into Dean’s mouth with a low moan.

Their movements begin to grow frantic the closer they get to their climax. The sound of skin slapping skin is both obscene and incredibly arousing. Dean pushes forward and drops his hands against the mirror.

Dean watches Cas’s face grow flushed and sweaty. His hair begins to stick to his brow with sweat and Dean’s climax approaches quicker at the picture they make in the mirror. His soul flairs brighter and bolder the closer he gets to his release.

Cas leans forward and intertwines the fingers of their left hands against the mirror. His right hands travels forward until it’s wrapped around Dean’s cock, stroking it in time with his thrusts.

Cas changes the angle slightly and suddenly he’s hitting Dean’s prostate every thrust. Dean’s muscles tense and he knows he’s going to come.

“Oh fuck! Cas!” He yells as the pleasure begins to get to be too much. He uses his tail to massage Cas’s prostate even harder and he feels the angel tense behind him before his ass is flooded with warm cum. That feeling is enough to send Dean over the edge. He paints his dresser with his cum and his soul becomes blindingly bright.

As they both slowly come down, Cas pulls out and Dean’s tail slides free. They both stumble over to the bed and lay down. Dean on his back with Cas laying across his chest. Dean idly strokes Cas’s feathers and they both begin to breathe normally again.

“I love you, Cas.” Dean says as his voice breaks. He clears his throat and begins again. “I honestly never thought I could feel this. I thought I would never feel love or joy or happiness but I do feel all those things. I’m still worried about my job getting in between us. I’m still afraid I might hurt you, Cas.”

Cas smiles his giant gummy smile at the demon and leans forward to kiss him. “ I trust you, Dean. And you have to trust that I’m far stronger than I look. Plus, I can help you. Did you see how when I touched you, your soul was brighter and stronger than the darkness inside you? We’re better together.”

Dean nods his head in agreement.

“No more running away?”

Dean smiles back, “No more running away. Promise.”

**Bonus scene:**

Gabe, Balthazar, Meg, Sam, and Charlie all stand just inside Gabe’s bedroom. All have a look of confusion and horror on their face.

The room is filled with feathers and bodily fluids and even a few dildos. The bedding is torn and thrown in all places. The bed is literally shredded down the middle and the pillows are torn and tossed everywhere.

“What the fuck did they do in here?” Gabe asks in horror.

Meg giggles and says, “I think it’s pretty obvious what they did. Hmm, didn’t know the little angel had this in him. I guess it took a demon to bring it out.”

Sam speaks up next, “I wouldn’t be laughing if I were you. So far they’ve hit my house, Balthazar’s, and now Gabe’s. I’m positive yours and Charlie’s are next and I really don’t wanna know what they have up their sleeves next.”

“Why’d this have to be their way of paying us back for meddling?” Charlie whines.

They all shrug. They thought the new couple would be happy for the help. Apparently not…

**Author's Note:**

> Come find us on Tumblr and say hi or give us more prompts!  
> [tobythewise](https://tobythewise.tumblr.com/)  
> [ladyofthursday](https://ladyofthursday.tumblr.com/)


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